Cyclopentaphenanthrene-based compound and organic electroluminescent device using the same

Abstract

Provided are a cyclopentaphenanthrene-based compound and an organic EL device using the same. The cyclopentaphenanthrene-based compound is easy to prepare and excellent in solubility, color purity, and color stability. The cyclopentaphenanthrene-based compound is useful as a material for forming an organic layer, in particular, a light-emitting layer in an organic EL device, and as an organic dye or an electronic material such as a nonlinear optical material.

1. An organic compound represented by Formula 1: 
       
         
           
           
               
               
           
         
         wherein Y and Q are the same or different and each is a substituted or unsubstituted C2-C30 alkylene group, a substituted or unsubstituted C6-C30 cycloalkylene group, a substituted or unsubstituted C6-C30 arylene group, a substituted or unsubstituted C2-C30 heteroarylene group, or a substituted or unsubstituted C2-C30 alkenylene group; 
         m=0; 
         n=0; 
         R 1  and R 2  are the same or different and each is a hydrogen, a halogen, a cyano group, a hydroxyl group, a substituted or unsubstituted C1-C20 alkyl group, a substituted or unsubstituted C3-C20 cycloalkyl group, a substituted or unsubstituted C2-C30 heterocycloalkyl group, a substituted or unsubstituted C1-C20 alkoxy group, a substituted or unsubstituted C6-C30 aryl group, a substituted or unsubstituted C6-C30 aralkyl group, a substituted or unsubstituted C2-C30 heteroaryl group, R 1  and R 2  may be linked together, and R 1  and R 2 , when linked together, form a substituted or unsubstituted C3-C20 aliphatic ring, a substituted or unsubstituted C5-C30 heteroaliphatic ring, a substituted or unsubstituted C6-C30 aromatic ring, or a substituted or unsubstituted C2-C30 heteroaromatic ring; 
         R 3 , R 4 , R 5 , R 6 , R 7 , and R 8  are the same or different and each is a hydrogen, a halogen, a cyano group, a hydroxyl group, a substituted or unsubstituted C1-C20 alkyl group, a substituted or unsubstituted C3-C20 cycloalkyl group, a substituted or unsubstituted C2-C30 heterocycloalkyl group, a substituted or unsubstituted C1-C20 alkoxy group, a substituted or unsubstituted C6-C30 aryl group, a substituted or unsubstituted C6-C30 aralkyl group, a substituted or unsubstituted C2-C30 heteroaryl group, —N(G 1 )(G 2 ), or —Si(G 3 )(G 4 )(G 5 ) where G 1 , G 2 , G 3 , G 4 , and G 5  are each independently a hydrogen, a substituted or unsubstituted C1-C20 alkyl group, a substituted or unsubstituted C6-C30 aryl group, a substituted or unsubstituted C2-C30 heteroaryl group, a substituted or unsubstituted C5-C20 cycloalkyl group, or a substituted or unsubstituted C2-C30 heterocycloalkyl group; 
         Z 1 , Z 2 , Z 3 , and Z 4  are the same or different and each is a substituted or unsubstituted C1-C20 alkyl group, a substituted or unsubstituted C3-C20 cycloalkyl group, a substituted or unsubstituted C2-C30 heterocycloalkyl group, a substituted or unsubstituted C1-C20 alkoxy group, a substituted or unsubstituted C6-C30 aryl group, a substituted or unsubstituted C2-C30 heteroaryl group, a substituted or unsubstituted C6-C30 aralkyl group, a substituted or unsubstituted C8-C30 allylaryl group, a substituted or unsubstituted C1-C20 alkylene group, a substituted or unsubstituted C6-C30 arylene group, or a substituted or unsubstituted C2-C30 heteroarylene group; 
         X is a single bond, —CH═CH—, —O—, —Se—, or —C(R′R″)— where R′ and R″ are the same as R 3 , or —(CH 2 ) p — where p is an integer of 1 to 10; and 
         o=0. 
       
     
     
       2. The organic compound of  claim 1 , wherein in Formula 1, R 1  and R 2 , when linked together, form one of rings represented by Formulae 2 through 5: 
       
         
           
           
               
               
           
         
         wherein “R 9 ”s are the same or different and each is a hydrogen, a halogen, a cyano group, a hydroxyl group, a substituted or unsubstituted C1-C20 alkyl group, a substituted or unsubstituted C3-C20 cycloalkyl group, a substituted or unsubstituted C2-C30 heterocycloalkyl group, a substituted or unsubstituted C1-C20 alkoxy group, a substituted or unsubstituted C6-C30 aryl group, a substituted or unsubstituted C6-C30 aralkyl group, a substituted or unsubstituted C2-C30 heteroaryl group, —N(G 1 )(G 2 ), or —Si(G 3 )(G 4 )(G 5 ) where G 1 , G 2 , G 3 , G 4 , and G 5  are each independently a hydrogen, a substituted or unsubstituted C1-C20 alkyl group, a substituted or unsubstituted C6-C30 aryl group, a substituted or unsubstituted C2-C30 heteroaryl group, a substituted or unsubstituted C5-C20 cycloalkyl group, or a substituted or unsubstituted C2-C30 heterocycloalkyl group; and 
         A is a single bond, —O—, —(CH 2 ) s —, where s is an integer of 1 to 5. 
       
     
     
       3. The organic compound of  claim 1 , which is selected from the group consisting of compounds represented by Formulae 6 through 8 below: 
       
         
           
           
               
               
           
         
         wherein Y and Q are the same or different and each is a substituted or unsubstituted C2-C30 alkylene group, a substituted or unsubstituted C6-C30 cycloalkylene group, a substituted or unsubstituted C6-C30 arylene group, a substituted or unsubstituted C2-C30 heteroarylene group, or a substituted or unsubstituted C2-C30 alkenylene group; 
         m=0; 
         n=0; 
         R 1 ′ and R 2 ′ are the same or different and each is a hydrogen, a halogen, a cyano group, a hydroxyl group, a substituted or unsubstituted C1-C20 alkyl group, a substituted or unsubstituted C3-C20 cycloalkyl group, a substituted or unsubstituted C2-C30 heterocycloalkyl group, a substituted or unsubstituted C1-C20 alkoxy group, a substituted or unsubstituted C6-C30 aryl group, a substituted or unsubstituted C6-C30 aralkyl group, a substituted or unsubstituted C2-C30 heteroaryl group; 
         Z 1 , Z 2 , Z 3 , and Z 4  are the same or different and each is a substituted or unsubstituted C1-C20 alkyl group, a substituted or unsubstituted C3-C20 cycloalkyl group, a substituted or unsubstituted C2-C30 heterocycloalkyl group, a substituted or unsubstituted C1-C20 alkoxy group, a substituted or unsubstituted C6-C30 aryl group, a substituted or unsubstituted C2-C30 heteroaryl group, a substituted or unsubstituted C6-C30 aralkyl group, a substituted or unsubstituted C2-C30 allylaryl group, a substituted or unsubstituted C1-C20 alkylene group, a substituted or unsubstituted C6-C30 arylene group, or a substituted or unsubstituted C2-C30 heteroarylene group; 
         X is a single bond, —CH═CH—, —O—, —S—, —Se—, or —C(R′, R″)— where R′ and R″ are the same as R 3 , or —(CH 2 ) p — where p is an integer of 1 to 10; 
         o=0; and 
         “R 10 ”s are the same or different and each is a hydrogen, a halogen, a cyano group, a hydroxyl group, a substituted or unsubstituted C1-C20 alkyl group, a substituted or unsubstituted C3-C20 cycloalkyl group, a substituted or unsubstituted C2-C30 heterocycloalkyl group, a substituted or unsubstituted C1-C20 alkoxy group, a substituted or unsubstituted C6-C30 aryl group, a substituted or unsubstituted C6-C30 aralkyl group, a substituted or unsubstituted C2-C30 heteroaryl group, —N(G 1 )(G 2 ), or —Si(G 3 )(G 4 )(G 5 ) where G 1 , G 2 , G 3 , G 4 , and G 5  are each independently a hydrogen, a substituted or unsubstituted C1-C20 alkyl group, a substituted or unsubstituted C6-C30 aryl group, a substituted or unsubstituted C2-C30 heteroaryl group, a substituted or unsubstituted C5-C20 cycloalkyl group, or a substituted or unsubstituted C2-C30 heterocycloalkyl group. 
       
     
     
       4. The organic compound of  claim 1 , which is one of compounds represented by Formulae 9, 10, 12, 16, 17, 22 through 36 and 40 through 46: